Matthew “Matty” Gregg ’00 was six years old when he first dreamed of being a transcontinental runner. The idea was sparked after he watched a biopic on Terry Fox, a Canadian amputee, who ran coast to coast in 1980 to raise money and awareness for cancer research.
Gregg let the idea simmer until Nov. 6, 2018, when, at the age of 40, he set out from Cupertino, California, on a nine-month, 5,425-mile epic adventure. His journey crossed 24 states, ending in Concord, New Hampshire, and included unexpected twists such as being mistaken for a highway bomber by Louisiana police, running through snowstorms and heatwaves, and adopting a stray kitten that followed him through a desolate town in Georgia.
Gregg was a manager and engineer at Apple for 13 years, leading the Apple Pay global team and developing internal and external training tools that are still in use at Apple retail stores. He decided to plot his run — and give his 18-month notice — in 2017 after surgery to repair a neck injury. “If I didn’t do it soon, I wouldn’t be healthy enough to do it at all,” he says, explaining that years of undertaking ultramarathons (50-mile and 100-mile races) and ultra-distance obstacle course racing had taken their toll.
A risk taker since he was young — a trait he attributes to his mother — Gregg says he wasn’t afraid to leave his comfortable life on the West Coast. “I’m not really afraid of change. This is something I wanted to do and need to do,” he says, referencing this famous quote from Apple founder Steve Jobs: “I think if you do something and it turns out pretty good, then you should go do something else wonderful, not dwell on it for too long. Just figure out what’s next.”
Gregg getting an escort as he prepares to cross the Boston Marathon finish line. Photo by Louie Despres
Gregg’s goal for the run was twofold: gather insight for a book he’s writing, “Democracy in America 2,” a continuation of Alexis de Tocqueville’s “Democracy in America,” which he first read as a political science major at Holy Cross, and raise awareness and money for the Firefighter Cancer Support Network (FCSN), a nationwide nonprofit that educates firefighters about cancer risks, mentors them during a cancer diagnosis and supports research.
His book, to be published this year, picks up where de Tocqueville left off, examining the impact of the Industrial Revolution, communications and technology on society and democracy. Gregg interviewed people in cities and towns across America and wrote a series of essays that draws comparisons and contrasts about their lifestyles and environments.
He also visited more than 200 firehouses along his route and raised nearly $140,000 for FCSN. Cancer caused 70% of line-of-duty deaths for career firefighters in 2016, according to the organization. Gregg first learned about the nonprofit on a training run with a fire chief in California and felt he could make an impact. “Holy Cross was a great influence for me, not just fundraising for this run, but being charitable in general,” he notes.
Word of Gregg’s adventure spread among the firefighter community, bringing many, like 35-year veteran firefighter Ted DePaolo, out to meet him. DePaolo retired in 2018 from the Milford, Massachusetts, fire department when his esophageal cancer spread and required surgeons to remove 65% of his stomach. His last days as a firefighter coincided with the first steps of Gregg’s journey.
“My mornings are tough, but I really wanted to thank him in person,” says DePaolo, who met Gregg at a Natick, Massachusetts, firehouse one July morning when Gregg’s run took him through central Massachusetts. Like other firefighters along the way, DePaolo shared with Gregg the toll cancer has taken on his firehouse and his family.
Gregg with retired firefighter Ted DePaolo in Milford, Massachusetts.
In 2018, TV station Boston 25 reported that nine Milford firefighters, including DePaolo, were either battling cancer or had passed away from it. “The money Matty raised will help a lot of my brother and sister firefighters battling this horrendous disease,” DePaolo says.
Gregg’s coast-to-coast trek raised awareness of occupational cancer “better than any ad campaign,” notes Russell Osgood, FCSN state director for New Hampshire and a lieutenant in the Portsmouth Fire Department. Firefighters have a 9% higher risk of being diagnosed with cancer and a 14% higher risk of dying from cancer than the general U.S. population, according to research by the CDC/National Institute for Occupational Health and Safety.
“Matty’s run will help us make sure we have enough tool kits for all the newly diagnosed firefighters and that we can expand our education programs and mentor network even further,” Osgood says. As part of his Massachusetts route, Gregg followed the Boston Marathon course from Hopkinton to Boston.
As a sign of gratitude, FCSN coordinated with Boston Engine 33 Ladder 15 to provide Gregg with a fire engine escort across the Boston Marathon finish line on Boylston Street.
Gregg, who ran through 31 pairs of sneakers by the time he finished in Concord on August 7, 2019, says he’s enjoyed putting his feet up, cuddling with his new kitten, Ash, and reflecting on his massive undertaking. He’s also starting to ruminate on his next big idea: running for office in Nashua, New Hampshire, his hometown and new residence (he recently purchased his childhood home).
“If you think you can do something way beyond the realm of possibility, do it, but afford yourself the time to do it right,” he says. “This trip wasn’t impulsive. If it were, we would have seen a lot more challenges along the way.”
Written by Sandra Gittlen for the Winter 2020 issue of Holy Cross Magazine.
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